1,2-Bis(dimethylphosphino)ethane
1,2-Bis(dimethylphosphino)ethane (dmpe) is a diphosphine ligand in coordination chemistry. It is a colorless, air-sensitive liquid that is soluble in organic solvents. With the formula (CH2PMe2)2 is used as a compact strongly basic spectator ligand (Me = methyl), Representative complexes include V(dmpe)2(BH4)2, Mn(dmpe)2(AlH4)2, Tc(dmpe)2(CO)2Cl, and Ni(dmpe)Cl2.[2]
Names | |
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IUPAC name
Ethane-1,2-diylbis(dimethylphosphane) | |
Other names
DMPE ethylenebis(dimethylphosphine) 1,2-Bis(dimethylphosphino)ethane | |
Identifiers | |
3D model (JSmol) |
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ChemSpider | |
ECHA InfoCard | 100.155.809 |
PubChem CID |
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CompTox Dashboard (EPA) |
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Properties | |
C6H16P2 | |
Molar mass | 150.142 g·mol−1 |
Density | 0.9 g/mL at 25 °C |
Boiling point | 180 °C (356 °F; 453 K) |
Hazards | |
GHS pictograms | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
Synthesis
It is synthesised by the reaction of methylmagnesium iodide with 1,2-bis(dichlorophosphino)ethane:[3]
- Cl2PCH2CH2PCl2 + 4 MeMgI → Me2PCH2CH2PMe2 + 4 MgICl
Alternatively it can be generated by alkylation of sodium dimethylphosphide.
The synthesis of dmpe from thiophosphoryl chloride has led to serious accidents and has been abandoned.[4]
Related ligands
Tetramethylethylenediamine is the diamine analogue of dmpe. Bis(dicyclohexylphosphino)ethane is a bulky analogue of dmpe, which offers the advantage of being a solid.
References
- Sigma-Aldrich Co., 1,2-Bis(dimethylphosphino)ethane. Retrieved on 2013-07-20.
- Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. ISBN 978-0-08-037941-8.
- R. J. Burt; J. Chatt; W. Hussain; G. J. Leigh (1979). "A convenient synthesis of 1,2-bis(dichlorophosphino)ethane, 1,2-bis(dimethylphosphino)ethane and 1,2-bis(diethylphosphino)ethane". J. Organomet. Chem. 182 (2): 203–6. doi:10.1016/S0022-328X(00)94383-3.
- Bercaw, J. E.; Parshall, G. W. (1985). "Preparation of Tetramethyldiphosphine Disulfide and Ethylenebis(Dimethylphosphine) (Dmpe)". Inorganic Syntheses. Inorganic Syntheses. 23. pp. 199–200. doi:10.1002/9780470132548.ch42. ISBN 9780470132548.}